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Benzodifuran type organic small molecule photovoltaic material as well as preparation method and application thereof

A technology of benzodifuran and photovoltaic materials, which is applied in the fields of photovoltaic power generation, organic chemistry, semiconductor/solid-state device manufacturing, etc., can solve the problems of few reports and achieve wide absorption spectrum, good photoelectric conversion characteristics, and good photoelectric conversion efficiency Effect

Active Publication Date: 2017-07-07
HUNAN UNIV OF ARTS & SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0002] Benzo[1,2-b; 3,4-b]difuran (BDF) has been well used as an electron donor in polymer solar cells, and it is a class of electron donor units with excellent performance [Bo Liu,Xuewen Chen,Yingping Zou,LuXiao,Xinjun Xu,Yuehui He,Lidong Li,and Yongfang Li.Macromolecules,2012,45,6896-6905.], but coupled with other electron acceptor units as electron donor Later applications in the field of small organic molecule solar cells are rarely reported in the literature

Method used

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  • Benzodifuran type organic small molecule photovoltaic material as well as preparation method and application thereof
  • Benzodifuran type organic small molecule photovoltaic material as well as preparation method and application thereof
  • Benzodifuran type organic small molecule photovoltaic material as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0054] Example 1 4,8-Diisooctyloxy-benzo(1,2-b; 4,5-b')-difuran-2,6-bis(2,5-Diisooctyl-3, Preparation of 6-furyl-2-diketopyrrolopyrrole) (M1)

[0055] Specific steps are as follows:

[0056] ①Synthesis of Compound 1

[0057] Mix benzodifuran-4,8-dione (1.88g, 10mmol), NaOH (6.0g, 150mmol) and zinc powder (1.43g, 22mmol) in 30mL of water, stir and reflux for 1 hour, add bromo Isooctane (3.86g, 20mmol) was refluxed for 2 hours, then zinc powder (0.2g, 3mmol) was added, and the reaction was continued overnight. Cool to room temperature, pour the mixture into water, extract with dichloromethane, wash the organic phase twice with water, dry over anhydrous magnesium sulfate, spin to dry the solvent, and pass the crude product through a silica gel column (petroleum ether is the eluent) to obtain a colorless oily liquid Compound 1 (2.19 g, yield 53%).

[0058] The NMR spectrum, mass spectrum and elemental analysis of compound 1 are as follows:

[0059] 1 H NMR (400MHz, CDCl 3 ,...

Embodiment 2

[0075] Example 2 4,8-Diisooctyloxy-benzo(1,2-b; 4,5-b')-difuran-2,6-bis(2,5-Diisooctyl-3, Preparation of 6-furyl-2-diketopyrrolopyrrole) (M1)

[0076] Specific steps are as follows:

[0077] ①Synthesis of Compound 1

[0078] Mix benzodifuran-4,8-dione (1.88g, 10mmol), NaOH (6.0g, 150mmol) and zinc powder (1.43g, 22mmol) in 30mL of water, stir and reflux for 1 hour, add bromo Isooctane (4.83g, 25mmol) was refluxed for 2 hours, then zinc powder (0.2g, 3mmol) was added, and the reaction was continued overnight. Cool to room temperature, pour the mixture into water, extract with dichloromethane, wash the organic phase twice with water, dry over anhydrous magnesium sulfate, spin to dry the solvent, and pass the crude product through a silica gel column (petroleum ether is the eluent) to obtain a colorless oily liquid Compound 1 (1.95 g, yield 47%).

[0079] The NMR spectrum, mass spectrum and elemental analysis of compound 1 are as follows:

[0080] 1 H NMR (400MHz, CDCl 3 ,...

Embodiment 3

[0096] Example 3 4,8-Diisooctyloxy-benzo(1,2-b; 4,5-b')-difuran-2,6-di(2,5-diisooctyl-3, Preparation of 6-furyl-2-diketopyrrolopyrrole) (M1)

[0097] ①Synthesis of Compound 1

[0098] Mix benzodifuran-4,8-dione (1.88g, 10mmol), NaOH (6.0g, 150mmol) and zinc powder (1.43g, 22mmol) in 30mL of water, stir and reflux for 1 hour, add bromo Isooctane (5.79g, 30mmol) was refluxed for 2 hours, and zinc powder (0.2g, 3mmol) was added, and the reaction was continued overnight. Cool to room temperature, pour the mixture into water, extract with dichloromethane, wash the organic phase twice with water, dry over anhydrous magnesium sulfate, spin to dry the solvent, and pass the crude product through a silica gel column (petroleum ether is the eluent) to obtain a colorless oily liquid Compound 1 (2.10 g, yield 51%).

[0099] The NMR spectrum, mass spectrum and elemental analysis of compound 1 are as follows:

[0100] 1 H NMR (400MHz, CDCl 3 ,ppm):7.87(m,2H),7.37(m,2H),4.72(t,4H),2.12(...

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Abstract

The invention discloses a benzodifuran organic small molecule photovoltaic material as well as a preparation method and application thereof. The preparation method comprises the steps of synthesizing a benzo[1,2-b;3,4-b]difuran (BDF) organic electron donor unit containing different alkoxy side chains, and linking the BDF unit with another electron donor unit diketopyrrolopyrrole (DPP) through a carbon-carbon single bond by virtue of a Stille coupling method, so as to obtain the BDF type organic small molecule photovoltaic material, wherein the structure of the BDF type organic small molecule photovoltaic material is represented by the formula (I). The organic small molecule photovoltaic material has a wide visible area absorption range, proper HOMO and LUMO energy levels and a relatively narrow band gap. An organic solar cell is prepared by taking organic molecules as an electron donor and PC61BM or taking an organic matter electron acceptor as an electron acceptor, the highest energy conversion efficiency of the organic solar cell can reach 5.0%, and the organic solar cell has good photoelectric conversion efficiency. The formula is as shown in the specification.

Description

technical field [0001] The invention relates to the technical field of photovoltaic materials, in particular to a benzodifuran organic small molecule photovoltaic material and its preparation method and application. Background technique [0002] Benzo[1,2-b; 3,4-b]difuran (BDF) has been well used as an electron donor in polymer solar cells, and it is a class of electron donor units with excellent performance [Bo Liu,Xuewen Chen,Yingping Zou,LuXiao,Xinjun Xu,Yuehui He,Lidong Li,and Yongfang Li.Macromolecules,2012,45,6896-6905.], but coupled with other electron acceptor units as electron donor Later applications in the field of small organic molecule solar cells are rarely reported in the literature. BDF has a condensed heterocyclic structure similar to that of benzo[1,2-b; 3,4-b]dithiophene (BDT), and BDT is used as an electron donor in organic small molecule solar cells, obtaining up to 5.8% Energy conversion efficiency [Yuze Lin, Lanchao Ma, Yongfang Li, Yunqi Liu, Daoben...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D519/00H01L51/46
CPCC07D519/00H10K85/653H10K85/6574H10K85/6572Y02E10/549
Inventor 刘波陈远道王晓波王钢刘骏周诗彪胡霞何敏
Owner HUNAN UNIV OF ARTS & SCI
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